Conversion of alkylolamides into oxazolines



Patented Feb. 25, 1947 UNITED, STATES PATENT OOFFICE CONVERSION OF ALKYLOLAMIDES INTO OXAZOLINES Emeric I. Valko, St. Johns, Quebec, Canada, as-' signor to The Richards Chemical Works, Incorporated, Jersey City, N. J a corporation of New Jersey [No Drawing. Application May 29, 1940,

a Serial No. 337,832

My invention relates to the conversion ofalkylolamides of a certain type Tinto complex .compounds which are soluble in acidulated waterand which, owing to their surface activity in'wate'r, arejuseful as wetting, dispersing and finishing agents in the textile industry, as flotation agents in the mining industry, and which also possess,

remarkable germicidal properties.

One object of my invention is to convert the amide into an aminoester, by detaching the acyl group from the nitrogen and linking it to the oxygen of the hydroxyl.

Another object of the invention is to produce heterocyclic ring compounds having side chains attached to two or more of their carbon atoms 1 Claim. (01. 260-307) and the conversion of such rings into the corresponding aminoesters and their acidulated water soluble salts.

I accomplish these and other objects, which i will become apparent as the description proceeds, generally, by a process includingthe step of dehydrating an alkylolamide having the following general formula:

where R2 is a, hydroxy alkyl group and R3 is a hydrogen atom, an alkyl group or hydroxyalkyl group. Compounds of this type are, for instance, tris (hydroxymethyl) aminomethane, 2-amino-2- methyl-1.3-propanediol, and 2-amino-2-ethyl- 1.3-propanediol.

The amides may be dehydrated by heating them, in the absence of condensing agents, to temperatures above 200 C.

According to a specific feature of my invention,

2 the dehydration of the amides. in question may also be efieeted by heating the alkylolamide in the absence of condensing agents and excess acids and in the presence of an inert medium er high boiling solvent, such as for instance toluene or xylene, to the boiling temperature of the mix-- ture and keeping it at this temperature until the amide has been converted into an oxazoline:

The water liberated by the reaction is removed from the reaction mixture by evaporating together with the solvent. 7

If tris(hydroxymethyl) amidomethanes are used as starting materials, the resulting compounds.

are derivatives of 4-bis(hydroxymethyl) A -oxazoline, and if the amide is obtained by the condensation of tris(hydroxymethyl) aminomethane with an aliphatic acid, the dehydration product is a 2-alky1 derivative of 4-bis(hydroxymethyl)- A -oxazoline.

If 2-amido-2-alkyl-1.3-propanedioles are used, the resulting compounds are derivatives of 4-9.1- kyl-4-hydroxymethyl-A -oxazoline.

The oxazolines obtained may be subjected to a further heating step with alkylating agents in order to introduce further side chains.

Example I gms. of tris(hydroxymethyl) aminomethane are heated in a distilling flask with 50 gms. acetic anhydride. The temperature of the liquid is raised gradually up to 230 C. Approximately 27 gms. of water distills over, indicatin that the final product, a viscous liquid, is the 2-methyl 4-bis(hydroxymethyl) A -oxazoline.

Example II 105 parts by weight of 2-amino-2-methyl-L3- propanediol and 280 parts by weight of stearic acid are mixed with parts by weight of xylene and the mixture is kept at boiling temperature. The overdistilled liquid separates in xylene and water and the xylene is continuously led back into the reaction mixture. During four hours The obtained product is a whitesolid which can be dissolved by boiling withaqueous acetic acid; The product is the salt of the nionoester HOCH:

C-NHfl' CH3 Ha CHaOOO- Example III I 120 parts by Weight of 2-amino-2-ethyl-L3- propanediol and 200parts 'by Weight of lauric acid are mixed with 150 parts by weight of xylene. The procedure follows the description of Example 11. The product obtained can be dissolved in boiling aqueous acetic acid and exhibits an excellent surface activity.

The new substances obtained in accordance withmy invention can be used in solidor liquid form or as aqueous and non-aqueous solutions alone or mixed with other materials. In addition tothe already mentioned uses, they can be employed with benefit incl-eaning, filling, sizing, desizing, impregnating, mercerizing, delustering, degummingstripping, felting, oiling, dyeing and printing of natural and synthetic textile material-s as wool,- cotton, silk, rayon, etc. They are further useful as plasticizers for-natural and synthetic rubbers and resins.

" 27 parts by weight of water distill over.

EMERIC I. VALKO.

7 REFERENCES CITED iiThe following 1 references are of record in the file of this patent:

UNITED STATES PATENTS 7 Number Name Date 2,181,534 Martin Nov. 28, 1939 2,151,788 Mauersberger Mar. 28, 1939 2,215,038 Hodgin Sept. 1'7, 1940 2,089,212 Kritchevsky Aug. 10, 1937 2,114,326 7 Adams Apr. '19, 1938 1,990,453 Hund etal' Feb. '5, .1935 1,805,355 f 'Bockmuhlfet al May 12 1931 2,173,058 Kritchevsky Sept. '12, 1939 1,934,309 Hoover -1 Nov. 7 1933 2,267,965 Wilson Dec. 30, 1941 2,155,877 Waldman Apr. 25,, 193.9 2,161,938 Sonn June 13, 1939 FOREIGN PATENTS Number Country Date 409,345 German Feb. 5, 1925 144,475 Swiss 1 .1.. Mar. 16, 1931 830,125 French May 9, 1,938

OTHER REFERENCES Journal American Chem'ical'Soc'iety, June 1935,

pages 1079-1080, 260-307.

Use of Solvents in Synthetic Organic Chemistry, McA-rdle 1925. Van N ostrand C0,, New York, pp. 9, 122 to 126. v 

